Synthesis of Multifunctionalized Thiazolidine‐4‐thiones via [2+2+1] Annulation of Isothiocyanates and CF<sub>3</sub>‐Imidoyl Sulfoxonium Ylides
Yuhao Ding, Hailin Guo, Jingwen Fan, Zhiyong Li, Guolin Cheng
Abstract
Abstract 2‐Iminothiazolidin‐4‐one, 5‐ethylidenethiazolidin‐4‐one, and thiazolidine‐4‐thione are all medicinally relevant structures. In this work, a NaSO 2 CF 3 ‐promoted [2+2+1] cascade annulation reaction of CF 3 ‐imidoyl sulfoxonium ylides and isothiocyanates was reported to synthesize a variety of decorated thiazolidine‐4‐thiones in 35–91% yields with exclusive stereoselectivity. The gram‐scale reaction and further chemoselective S ‐alkylations demonstrated the synthetic utilities of this transformation.
Topics & Concepts
AnnulationChemistryThiazolidineCombinatorial chemistryStereoselectivityStereochemistryOrganic chemistryCatalysisSulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods